# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pv110
_database_code_depnum_ccdc_archive 'CCDC 1057223'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (E)-3-(3-bromo-4-(dimethylamino)phenyl)-1-(3-chloro-4-methoxyphenyl)prop-2-en-1-one
;
_chemical_name_common            
(E)-3-(3-bromo-4-(dimethylamino)phenyl)-1-(3-chloro-4-methoxyphenyl)prop-2-en-1-one
_chemical_melting_point          398-400
_chemical_formula_moiety         'C18 H17 Br Cl N O2'
_chemical_formula_sum            'C18 H17 Br Cl N O2'
_chemical_formula_weight         394.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.4151(8)
_cell_length_b                   7.5086(4)
_cell_length_c                   31.8698(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.194(2)
_cell_angle_gamma                90.00
_cell_volume                     3405.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    2.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3067
_exptl_absorpt_correction_T_max  0.9038
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  20
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            74679
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         28.33
_reflns_number_total             8422
_reflns_number_gt                6536
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0367P)²+1.8695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8422
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br02 Br 0.626957(18) 0.48325(3) 0.065906(7) 0.03380(7) Uani 1 1 d . . .
Br01 Br 0.539401(18) -0.76221(3) -0.307920(7) 0.03455(7) Uani 1 1 d . . .
Cl01 Cl 0.89550(4) -0.35500(9) 0.064613(16) 0.03488(14) Uani 1 1 d . . .
Cl02 Cl 0.40156(5) -0.18208(9) -0.304857(17) 0.03901(15) Uani 1 1 d . . .
O04 O 0.35066(11) -0.4994(2) -0.26435(5) 0.0340(4) Uani 1 1 d . . .
O01 O 0.65185(10) -0.4233(2) -0.07525(5) 0.0293(3) Uani 1 1 d . . .
O03 O 0.51491(12) 0.1851(2) -0.16552(5) 0.0345(4) Uani 1 1 d . . .
C03 C 0.97695(14) -0.2690(3) -0.00378(7) 0.0227(4) Uani 1 1 d . . .
C02 C 0.89432(15) -0.3248(3) 0.01063(6) 0.0220(4) Uani 1 1 d . . .
N01 N 0.64411(13) -0.4479(3) -0.34307(5) 0.0266(4) Uani 1 1 d . . .
C01 C 0.81286(14) -0.3544(3) -0.01718(6) 0.0209(4) Uani 1 1 d . . .
H01 H 0.7579 -0.3915 -0.0067 0.025 Uiso 1 1 calc R . .
C11 C 0.59803(14) -0.5575(3) -0.23439(6) 0.0214(4) Uani 1 1 d . . .
H11 H 0.5658 -0.6466 -0.2212 0.026 Uiso 1 1 calc R . .
O02 O 1.05357(10) -0.2436(2) 0.02614(5) 0.0295(3) Uani 1 1 d . . .
C06 C 0.81009(15) -0.3304(3) -0.06087(6) 0.0226(4) Uani 1 1 d . . .
C29 C 0.60441(15) 0.2739(3) -0.00784(7) 0.0232(4) Uani 1 1 d . . .
H29 H 0.5856 0.3845 -0.0210 0.028 Uiso 1 1 calc R . .
C20 C 0.41873(15) -0.2179(3) -0.25037(7) 0.0251(5) Uani 1 1 d . . .
C30 C 0.63654(14) 0.2682(3) 0.03529(7) 0.0220(4) Uani 1 1 d . . .
C14 C 0.68569(16) -0.2945(3) -0.27420(7) 0.0291(5) Uani 1 1 d . . .
H14 H 0.7144 -0.2012 -0.2876 0.035 Uiso 1 1 calc R . .
C07 C 0.72035(15) -0.3690(3) -0.08979(6) 0.0231(4) Uani 1 1 d . . .
C28 C 0.59911(14) 0.1188(3) -0.03252(6) 0.0222(4) Uani 1 1 d . . .
C22 C 0.40148(15) -0.4055(3) -0.19128(7) 0.0266(5) Uani 1 1 d . . .
H22 H 0.3819 -0.5140 -0.1801 0.032 Uiso 1 1 calc R . .
C33 C 0.62731(15) -0.0399(3) -0.01182(7) 0.0256(5) Uani 1 1 d . . .
H33 H 0.6220 -0.1481 -0.0275 0.031 Uiso 1 1 calc R . .
C12 C 0.59715(14) -0.5623(3) -0.27786(6) 0.0216(4) Uani 1 1 d . . .
C31 C 0.67000(14) 0.1111(3) 0.05623(6) 0.0220(4) Uani 1 1 d . . .
C10 C 0.64595(14) -0.4227(3) -0.20984(6) 0.0219(4) Uani 1 1 d . . .
C26 C 0.54343(15) -0.0013(3) -0.10551(7) 0.0254(4) Uani 1 1 d . . .
H26 H 0.5494 -0.1208 -0.0957 0.030 Uiso 1 1 calc R . .
N02 N 0.70545(12) 0.1085(2) 0.09998(5) 0.0261(4) Uani 1 1 d . . .
C25 C 0.51066(15) 0.0346(3) -0.15103(7) 0.0244(4) Uani 1 1 d . . .
C13 C 0.64172(14) -0.4333(3) -0.29887(6) 0.0224(4) Uani 1 1 d . . .
C19 C 0.45905(14) -0.0879(3) -0.22318(6) 0.0239(4) Uani 1 1 d . . .
H19 H 0.4789 0.0205 -0.2343 0.029 Uiso 1 1 calc R . .
C23 C 0.44213(15) -0.2738(3) -0.16388(7) 0.0251(4) Uani 1 1 d . . .
H23 H 0.4502 -0.2935 -0.1341 0.030 Uiso 1 1 calc R . .
C09 C 0.65330(14) -0.4301(3) -0.16364(6) 0.0227(4) Uani 1 1 d . . .
H09 H 0.6090 -0.5021 -0.1524 0.027 Uiso 1 1 calc R . .
C15 C 0.68845(16) -0.2895(3) -0.23060(7) 0.0275(5) Uani 1 1 d . . .
H15 H 0.7197 -0.1941 -0.2146 0.033 Uiso 1 1 calc R . .
C32 C 0.66293(15) -0.0430(3) 0.03111(7) 0.0256(5) Uani 1 1 d . . .
H32 H 0.6833 -0.1532 0.0440 0.031 Uiso 1 1 calc R . .
C21 C 0.38931(14) -0.3799(3) -0.23484(7) 0.0254(5) Uani 1 1 d . . .
C05 C 0.89178(16) -0.2748(3) -0.07516(7) 0.0285(5) Uani 1 1 d . . .
H05 H 0.8912 -0.2575 -0.1047 0.034 Uiso 1 1 calc R . .
C08 C 0.71712(15) -0.3440(3) -0.13578(6) 0.0246(4) Uani 1 1 d . . .
H08 H 0.7607 -0.2661 -0.1458 0.029 Uiso 1 1 calc R . .
C16 C 1.13816(16) -0.1857(3) 0.01211(8) 0.0340(5) Uani 1 1 d . . .
H16A H 1.1562 -0.2722 -0.0081 0.051 Uiso 1 1 calc R . .
H16B H 1.1885 -0.1759 0.0366 0.051 Uiso 1 1 calc R . .
H16C H 1.1276 -0.0692 -0.0017 0.051 Uiso 1 1 calc R . .
C24 C 0.47116(14) -0.1139(3) -0.17920(6) 0.0218(4) Uani 1 1 d . . .
C27 C 0.56470(14) 0.1323(3) -0.07804(6) 0.0240(4) Uani 1 1 d . . .
H27 H 0.5565 0.2492 -0.0894 0.029 Uiso 1 1 calc R . .
C04 C 0.97393(15) -0.2444(3) -0.04698(7) 0.0285(5) Uani 1 1 d . . .
H04 H 1.0287 -0.2062 -0.0575 0.034 Uiso 1 1 calc R . .
C34 C 0.32696(19) -0.6699(3) -0.24893(9) 0.0418(6) Uani 1 1 d . . .
H34A H 0.3831 -0.7241 -0.2324 0.063 Uiso 1 1 calc R . .
H34B H 0.3029 -0.7471 -0.2730 0.063 Uiso 1 1 calc R . .
H34C H 0.2787 -0.6553 -0.2308 0.063 Uiso 1 1 calc R . .
C36 C 0.71130(18) -0.0652(3) 0.12078(7) 0.0347(5) Uani 1 1 d . . .
H36A H 0.6515 -0.1283 0.1131 0.052 Uiso 1 1 calc R . .
H36B H 0.7245 -0.0490 0.1517 0.052 Uiso 1 1 calc R . .
H36C H 0.7619 -0.1350 0.1116 0.052 Uiso 1 1 calc R . .
C18 C 0.72566(18) -0.3660(4) -0.35744(8) 0.0417(6) Uani 1 1 d . . .
H18A H 0.7174 -0.2365 -0.3589 0.062 Uiso 1 1 calc R . .
H18B H 0.7317 -0.4118 -0.3857 0.062 Uiso 1 1 calc R . .
H18C H 0.7826 -0.3950 -0.3374 0.062 Uiso 1 1 calc R . .
C35 C 0.79069(19) 0.2132(4) 0.11375(9) 0.0485(7) Uani 1 1 d . . .
H35A H 0.8461 0.1417 0.1106 0.073 Uiso 1 1 calc R . .
H35B H 0.7935 0.2472 0.1436 0.073 Uiso 1 1 calc R . .
H35C H 0.7895 0.3207 0.0962 0.073 Uiso 1 1 calc R . .
C17 C 0.55712(18) -0.3883(4) -0.36925(7) 0.0369(6) Uani 1 1 d . . .
H17A H 0.5036 -0.4493 -0.3602 0.055 Uiso 1 1 calc R . .
H17B H 0.5591 -0.4163 -0.3991 0.055 Uiso 1 1 calc R . .
H17C H 0.5503 -0.2594 -0.3660 0.055 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br02 C30 1.903(2) . ?
Br01 C12 1.900(2) . ?
Cl01 C02 1.733(2) . ?
Cl02 C20 1.735(2) . ?
O04 C21 1.354(3) . ?
O04 C34 1.432(3) . ?
O01 C07 1.226(3) . ?
O03 C25 1.226(3) . ?
C03 O02 1.352(3) . ?
C03 C04 1.383(3) . ?
C03 C02 1.407(3) . ?
C02 C01 1.372(3) . ?
N01 C13 1.419(3) . ?
N01 C17 1.461(3) . ?
N01 C18 1.463(3) . ?
C01 C06 1.398(3) . ?
C01 H01 0.9500 . ?
C11 C12 1.384(3) . ?
C11 C10 1.393(3) . ?
C11 H11 0.9500 . ?
O02 C16 1.432(3) . ?
C06 C05 1.393(3) . ?
C06 C07 1.492(3) . ?
C29 C30 1.379(3) . ?
C29 C28 1.401(3) . ?
C29 H29 0.9500 . ?
C20 C19 1.371(3) . ?
C20 C21 1.404(3) . ?
C30 C31 1.403(3) . ?
C14 C15 1.384(3) . ?
C14 C13 1.395(3) . ?
C14 H14 0.9500 . ?
C07 C08 1.471(3) . ?
C28 C33 1.391(3) . ?
C28 C27 1.460(3) . ?
C22 C21 1.384(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C33 C32 1.382(3) . ?
C33 H33 0.9500 . ?
C12 C13 1.391(3) . ?
C31 C32 1.401(3) . ?
C31 N02 1.406(3) . ?
C10 C15 1.394(3) . ?
C10 C09 1.460(3) . ?
C26 C27 1.334(3) . ?
C26 C25 1.477(3) . ?
C26 H26 0.9500 . ?
N02 C36 1.459(3) . ?
N02 C35 1.466(3) . ?
C25 C24 1.486(3) . ?
C19 C24 1.398(3) . ?
C19 H19 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C09 C08 1.338(3) . ?
C09 H09 0.9500 . ?
C15 H15 0.9500 . ?
C32 H32 0.9500 . ?
C05 C04 1.386(3) . ?
C05 H05 0.9500 . ?
C08 H08 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C27 H27 0.9500 . ?
C04 H04 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O04 C34 116.65(18) . . ?
O02 C03 C04 125.14(19) . . ?
O02 C03 C02 116.77(18) . . ?
C04 C03 C02 118.10(19) . . ?
C01 C02 C03 121.29(18) . . ?
C01 C02 Cl01 119.48(16) . . ?
C03 C02 Cl01 119.24(16) . . ?
C13 N01 C17 112.86(17) . . ?
C13 N01 C18 115.24(18) . . ?
C17 N01 C18 110.60(19) . . ?
C02 C01 C06 120.52(19) . . ?
C02 C01 H01 119.7 . . ?
C06 C01 H01 119.7 . . ?
C12 C11 C10 120.37(19) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C03 O02 C16 117.57(17) . . ?
C05 C06 C01 118.24(19) . . ?
C05 C06 C07 123.45(19) . . ?
C01 C06 C07 118.30(19) . . ?
C30 C29 C28 120.89(19) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C19 C20 C21 121.00(19) . . ?
C19 C20 Cl02 120.03(17) . . ?
C21 C20 Cl02 118.96(16) . . ?
C29 C30 C31 122.38(19) . . ?
C29 C30 Br02 116.39(15) . . ?
C31 C30 Br02 121.15(15) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
O01 C07 C08 121.33(19) . . ?
O01 C07 C06 120.16(18) . . ?
C08 C07 C06 118.49(18) . . ?
C33 C28 C29 117.41(18) . . ?
C33 C28 C27 123.93(19) . . ?
C29 C28 C27 118.66(18) . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C32 C33 C28 121.2(2) . . ?
C32 C33 H33 119.4 . . ?
C28 C33 H33 119.4 . . ?
C11 C12 C13 122.18(19) . . ?
C11 C12 Br01 117.28(15) . . ?
C13 C12 Br01 120.40(15) . . ?
C32 C31 C30 115.74(18) . . ?
C32 C31 N02 122.47(19) . . ?
C30 C31 N02 121.76(18) . . ?
C11 C10 C15 118.07(19) . . ?
C11 C10 C09 119.24(19) . . ?
C15 C10 C09 122.64(19) . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C31 N02 C36 116.63(18) . . ?
C31 N02 C35 116.34(18) . . ?
C36 N02 C35 111.02(19) . . ?
O03 C25 C26 120.72(19) . . ?
O03 C25 C24 120.07(19) . . ?
C26 C25 C24 119.21(18) . . ?
C12 C13 C14 116.85(19) . . ?
C12 C13 N01 120.69(19) . . ?
C14 C13 N01 122.43(19) . . ?
C20 C19 C24 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C24 C19 H19 119.8 . . ?
C22 C23 C24 121.2(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C08 C09 C10 125.6(2) . . ?
C08 C09 H09 117.2 . . ?
C10 C09 H09 117.2 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C33 C32 C31 122.23(19) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
O04 C21 C22 125.2(2) . . ?
O04 C21 C20 116.31(19) . . ?
C22 C21 C20 118.48(19) . . ?
C04 C05 C06 121.1(2) . . ?
C04 C05 H05 119.4 . . ?
C06 C05 H05 119.4 . . ?
C09 C08 C07 120.6(2) . . ?
C09 C08 H08 119.7 . . ?
C07 C08 H08 119.7 . . ?
O02 C16 H16A 109.5 . . ?
O02 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O02 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C23 C24 C19 118.51(19) . . ?
C23 C24 C25 123.04(19) . . ?
C19 C24 C25 118.39(18) . . ?
C26 C27 C28 127.3(2) . . ?
C26 C27 H27 116.4 . . ?
C28 C27 H27 116.4 . . ?
C03 C04 C05 120.7(2) . . ?
C03 C04 H04 119.6 . . ?
C05 C04 H04 119.6 . . ?
O04 C34 H34A 109.5 . . ?
O04 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O04 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N02 C36 H36A 109.5 . . ?
N02 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N02 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N01 C18 H18A 109.5 . . ?
N01 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N01 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N02 C35 H35A 109.5 . . ?
N02 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N02 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N01 C17 H17A 109.5 . . ?
N01 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N01 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O02 C03 C02 C01 -179.93(18) . . . . ?
C04 C03 C02 C01 0.0(3) . . . . ?
O02 C03 C02 Cl01 0.6(3) . . . . ?
C04 C03 C02 Cl01 -179.44(16) . . . . ?
C03 C02 C01 C06 0.3(3) . . . . ?
Cl01 C02 C01 C06 179.78(16) . . . . ?
C04 C03 O02 C16 0.4(3) . . . . ?
C02 C03 O02 C16 -179.62(19) . . . . ?
C02 C01 C06 C05 -0.4(3) . . . . ?
C02 C01 C06 C07 178.43(19) . . . . ?
C28 C29 C30 C31 3.5(3) . . . . ?
C28 C29 C30 Br02 -173.25(16) . . . . ?
C05 C06 C07 O01 177.5(2) . . . . ?
C01 C06 C07 O01 -1.3(3) . . . . ?
C05 C06 C07 C08 -1.2(3) . . . . ?
C01 C06 C07 C08 -179.96(19) . . . . ?
C30 C29 C28 C33 0.1(3) . . . . ?
C30 C29 C28 C27 -179.92(19) . . . . ?
C29 C28 C33 C32 -2.7(3) . . . . ?
C27 C28 C33 C32 177.30(19) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C10 C11 C12 Br01 174.63(15) . . . . ?
C29 C30 C31 C32 -4.1(3) . . . . ?
Br02 C30 C31 C32 172.42(15) . . . . ?
C29 C30 C31 N02 177.86(19) . . . . ?
Br02 C30 C31 N02 -5.6(3) . . . . ?
C12 C11 C10 C15 3.1(3) . . . . ?
C12 C11 C10 C09 -174.24(19) . . . . ?
C32 C31 N02 C36 -16.0(3) . . . . ?
C30 C31 N02 C36 161.9(2) . . . . ?
C32 C31 N02 C35 118.1(2) . . . . ?
C30 C31 N02 C35 -64.0(3) . . . . ?
C27 C26 C25 O03 10.4(3) . . . . ?
C27 C26 C25 C24 -168.90(19) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
Br01 C12 C13 C14 -177.46(16) . . . . ?
C11 C12 C13 N01 176.28(19) . . . . ?
Br01 C12 C13 N01 0.6(3) . . . . ?
C15 C14 C13 C12 2.8(3) . . . . ?
C15 C14 C13 N01 -175.2(2) . . . . ?
C17 N01 C13 C12 80.5(3) . . . . ?
C18 N01 C13 C12 -151.1(2) . . . . ?
C17 N01 C13 C14 -101.6(2) . . . . ?
C18 N01 C13 C14 26.8(3) . . . . ?
C21 C20 C19 C24 -0.4(3) . . . . ?
Cl02 C20 C19 C24 178.49(16) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C11 C10 C09 C08 159.7(2) . . . . ?
C15 C10 C09 C08 -17.5(3) . . . . ?
C13 C14 C15 C10 -0.9(4) . . . . ?
C11 C10 C15 C14 -2.1(3) . . . . ?
C09 C10 C15 C14 175.2(2) . . . . ?
C28 C33 C32 C31 1.9(3) . . . . ?
C30 C31 C32 C33 1.4(3) . . . . ?
N02 C31 C32 C33 179.45(19) . . . . ?
C34 O04 C21 C22 -4.7(3) . . . . ?
C34 O04 C21 C20 175.5(2) . . . . ?
C23 C22 C21 O04 179.9(2) . . . . ?
C23 C22 C21 C20 -0.2(3) . . . . ?
C19 C20 C21 O04 -179.80(19) . . . . ?
Cl02 C20 C21 O04 1.3(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
Cl02 C20 C21 C22 -178.61(16) . . . . ?
C01 C06 C05 C04 0.2(3) . . . . ?
C07 C06 C05 C04 -178.6(2) . . . . ?
C10 C09 C08 C07 -176.96(19) . . . . ?
O01 C07 C08 C09 -21.5(3) . . . . ?
C06 C07 C08 C09 157.1(2) . . . . ?
C22 C23 C24 C19 -0.3(3) . . . . ?
C22 C23 C24 C25 176.85(19) . . . . ?
C20 C19 C24 C23 0.4(3) . . . . ?
C20 C19 C24 C25 -176.89(19) . . . . ?
O03 C25 C24 C23 -163.1(2) . . . . ?
C26 C25 C24 C23 16.1(3) . . . . ?
O03 C25 C24 C19 14.1(3) . . . . ?
C26 C25 C24 C19 -166.68(18) . . . . ?
C25 C26 C27 C28 -178.99(19) . . . . ?
C33 C28 C27 C26 9.2(3) . . . . ?
C29 C28 C27 C26 -170.8(2) . . . . ?
O02 C03 C04 C05 179.7(2) . . . . ?
C02 C03 C04 C05 -0.3(3) . . . . ?
C06 C05 C04 C03 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.079
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pv111
_database_code_depnum_ccdc_archive 'CCDC 1057224'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (E)-3-(3-chloro-4-(dimethylamino)phenyl)-1-(3-chloro-4-methoxyphenyl)prop-2-en-1-one
;
_chemical_name_common            
(E)-3-(3-chloro-4-(dimethylamino)phenyl)-1-(3-chloro-4-methoxyphenyl)prop-2-en-1-one
_chemical_melting_point          384-386
_chemical_formula_moiety         'C18 H17 Cl2 N O2'
_chemical_formula_sum            'C18 H17 Cl2 N O2'
_chemical_formula_weight         350.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.4606(6)
_cell_length_b                   7.4161(3)
_cell_length_c                   31.6780(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.798(2)
_cell_angle_gamma                90.00
_cell_volume                     3365.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8909
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0.5
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            61721
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         26.44
_reflns_number_total             6915
_reflns_number_gt                5146
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0359P)²+2.0246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6915
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl03 Cl 0.40355(4) 0.17469(8) 0.194948(15) 0.04031(15) Uani 1 1 d . . .
Cl01 Cl 0.88878(3) -0.65815(8) 0.561674(14) 0.03525(14) Uani 1 1 d . . .
Cl04 Cl 0.62805(4) -0.47020(7) 0.564368(16) 0.03901(15) Uani 1 1 d . . .
Cl02 Cl 0.53280(4) -0.26213(8) 0.191462(16) 0.03803(14) Uani 1 1 d . . .
O01 O 0.65143(9) -0.57449(19) 0.42238(4) 0.0304(3) Uani 1 1 d . . .
O02 O 1.04848(9) -0.7598(2) 0.52172(4) 0.0306(3) Uani 1 1 d . . .
N01 N 0.64034(11) -0.5510(2) 0.15264(5) 0.0275(4) Uani 1 1 d . . .
O04 O 0.34976(10) 0.4963(2) 0.23550(4) 0.0352(3) Uani 1 1 d . . .
O03 O 0.51614(11) -0.18983(19) 0.33454(4) 0.0370(4) Uani 1 1 d . . .
C28 C 0.59783(13) -0.1205(3) 0.46767(6) 0.0243(4) Uani 1 1 d . . .
C07 C 0.72081(13) -0.6256(3) 0.40725(6) 0.0246(4) Uani 1 1 d . . .
C01 C 0.81034(13) -0.6445(2) 0.47976(6) 0.0227(4) Uani 1 1 d . . .
H01 H 0.7550 -0.6097 0.4907 0.027 Uiso 1 1 calc R . .
C10 C 0.64648(13) -0.5765(3) 0.28690(6) 0.0227(4) Uani 1 1 d . . .
C23 C 0.44301(13) 0.2748(3) 0.33617(6) 0.0261(4) Uani 1 1 d . . .
H23 H 0.4513 0.2963 0.3660 0.031 Uiso 1 1 calc R . .
N02 N 0.70208(11) -0.1067(2) 0.59976(5) 0.0292(4) Uani 1 1 d . . .
C09 C 0.65414(13) -0.5683(3) 0.33341(6) 0.0237(4) Uani 1 1 d . . .
H09 H 0.6090 -0.4978 0.3451 0.028 Uiso 1 1 calc R . .
C19 C 0.46109(13) 0.0844(3) 0.27670(6) 0.0255(4) Uani 1 1 d . . .
H19 H 0.4818 -0.0251 0.2655 0.031 Uiso 1 1 calc R . .
C11 C 0.59481(13) -0.4451(3) 0.26275(6) 0.0228(4) Uani 1 1 d . . .
H11 H 0.5611 -0.3578 0.2764 0.027 Uiso 1 1 calc R . .
C03 C 0.97380(13) -0.7278(3) 0.49212(6) 0.0232(4) Uani 1 1 d . . .
C13 C 0.63967(13) -0.5669(3) 0.19722(6) 0.0237(4) Uani 1 1 d . . .
C22 C 0.40133(13) 0.4059(3) 0.30876(6) 0.0278(4) Uani 1 1 d . . .
H22 H 0.3808 0.5155 0.3199 0.033 Uiso 1 1 calc R . .
C32 C 0.66039(14) 0.0455(3) 0.53085(6) 0.0278(4) Uani 1 1 d . . .
H32 H 0.6799 0.1576 0.5436 0.033 Uiso 1 1 calc R . .
C31 C 0.66794(13) -0.1103(3) 0.55608(6) 0.0251(4) Uani 1 1 d . . .
C20 C 0.41992(13) 0.2138(3) 0.24956(6) 0.0253(4) Uani 1 1 d . . .
C25 C 0.51218(13) -0.0366(3) 0.34917(6) 0.0258(4) Uani 1 1 d . . .
C24 C 0.47285(13) 0.1123(3) 0.32080(6) 0.0233(4) Uani 1 1 d . . .
C33 C 0.62558(13) 0.0417(3) 0.48808(6) 0.0276(4) Uani 1 1 d . . .
H33 H 0.6204 0.1509 0.4723 0.033 Uiso 1 1 calc R . .
C08 C 0.71863(13) -0.6508(3) 0.36090(6) 0.0263(4) Uani 1 1 d . . .
H08 H 0.7636 -0.7264 0.3505 0.032 Uiso 1 1 calc R . .
C02 C 0.89027(13) -0.6775(3) 0.50710(5) 0.0227(4) Uani 1 1 d . . .
C06 C 0.80974(13) -0.6616(3) 0.43580(6) 0.0233(4) Uani 1 1 d . . .
C29 C 0.60327(13) -0.2761(3) 0.49253(6) 0.0264(4) Uani 1 1 d . . .
H29 H 0.5847 -0.3883 0.4796 0.032 Uiso 1 1 calc R . .
C26 C 0.54405(13) 0.0005(3) 0.39448(6) 0.0261(4) Uani 1 1 d . . .
H26 H 0.5503 0.1218 0.4041 0.031 Uiso 1 1 calc R . .
C30 C 0.63522(13) -0.2703(3) 0.53564(6) 0.0252(4) Uani 1 1 d . . .
C27 C 0.56433(13) -0.1343(3) 0.42218(6) 0.0265(4) Uani 1 1 d . . .
H27 H 0.5560 -0.2529 0.4110 0.032 Uiso 1 1 calc R . .
C14 C 0.68810(14) -0.7009(3) 0.22170(6) 0.0319(5) Uani 1 1 d . . .
H14 H 0.7193 -0.7917 0.2079 0.038 Uiso 1 1 calc R . .
C21 C 0.38955(13) 0.3771(3) 0.26492(6) 0.0275(4) Uani 1 1 d . . .
C12 C 0.59227(13) -0.4409(3) 0.21899(6) 0.0234(4) Uani 1 1 d . . .
C04 C 0.97322(14) -0.7421(3) 0.44856(6) 0.0298(5) Uani 1 1 d . . .
H04 H 1.0288 -0.7747 0.4375 0.036 Uiso 1 1 calc R . .
C15 C 0.69221(14) -0.7060(3) 0.26551(6) 0.0317(5) Uani 1 1 d . . .
H15 H 0.7266 -0.7988 0.2812 0.038 Uiso 1 1 calc R . .
C16 C 1.13336(14) -0.8158(3) 0.50663(7) 0.0349(5) Uani 1 1 d . . .
H16A H 1.1226 -0.9294 0.4909 0.052 Uiso 1 1 calc R . .
H16B H 1.1822 -0.8331 0.5309 0.052 Uiso 1 1 calc R . .
H16C H 1.1531 -0.7230 0.4877 0.052 Uiso 1 1 calc R . .
C05 C 0.89233(14) -0.7093(3) 0.42086(6) 0.0297(5) Uani 1 1 d . . .
H05 H 0.8934 -0.7197 0.3910 0.036 Uiso 1 1 calc R . .
C35 C 0.70858(16) 0.0691(3) 0.62066(6) 0.0385(6) Uani 1 1 d . . .
H35A H 0.7612 0.1364 0.6120 0.058 Uiso 1 1 calc R . .
H35B H 0.7182 0.0524 0.6516 0.058 Uiso 1 1 calc R . .
H35C H 0.6507 0.1364 0.6123 0.058 Uiso 1 1 calc R . .
C34 C 0.32496(17) 0.6693(3) 0.25082(8) 0.0439(6) Uani 1 1 d . . .
H34A H 0.2764 0.6544 0.2693 0.066 Uiso 1 1 calc R . .
H34B H 0.3014 0.7464 0.2266 0.066 Uiso 1 1 calc R . .
H34C H 0.3801 0.7254 0.2670 0.066 Uiso 1 1 calc R . .
C17 C 0.72169(16) -0.6288(3) 0.13646(7) 0.0429(6) Uani 1 1 d . . .
H17A H 0.7785 -0.5957 0.1554 0.064 Uiso 1 1 calc R . .
H17B H 0.7253 -0.5824 0.1078 0.064 Uiso 1 1 calc R . .
H17C H 0.7157 -0.7604 0.1354 0.064 Uiso 1 1 calc R . .
C36 C 0.78357(17) -0.2184(4) 0.61396(7) 0.0517(7) Uani 1 1 d . . .
H36A H 0.7814 -0.3279 0.5965 0.078 Uiso 1 1 calc R . .
H36B H 0.7835 -0.2515 0.6439 0.078 Uiso 1 1 calc R . .
H36C H 0.8405 -0.1508 0.6110 0.078 Uiso 1 1 calc R . .
C18 C 0.55420(15) -0.6134(3) 0.12742(6) 0.0373(5) Uani 1 1 d . . .
H18C H 0.5493 -0.7446 0.1301 0.056 Uiso 1 1 calc R . .
H18A H 0.5549 -0.5816 0.0974 0.056 Uiso 1 1 calc R . .
H18B H 0.5006 -0.5559 0.1378 0.056 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl03 C20 1.7386(19) . ?
Cl01 C02 1.7377(18) . ?
Cl04 C30 1.750(2) . ?
Cl02 C12 1.7475(19) . ?
O01 C07 1.229(2) . ?
O02 C03 1.352(2) . ?
O02 C16 1.438(2) . ?
N01 C13 1.418(2) . ?
N01 C18 1.461(3) . ?
N01 C17 1.464(3) . ?
O04 C21 1.355(2) . ?
O04 C34 1.435(3) . ?
O03 C25 1.231(2) . ?
C28 C29 1.394(3) . ?
C28 C33 1.398(3) . ?
C28 C27 1.460(3) . ?
C07 C08 1.476(3) . ?
C07 C06 1.493(3) . ?
C01 C02 1.369(3) . ?
C01 C06 1.397(2) . ?
C01 H01 0.9500 . ?
C10 C11 1.392(3) . ?
C10 C15 1.393(3) . ?
C10 C09 1.464(2) . ?
C23 C22 1.386(3) . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
N02 C31 1.405(2) . ?
N02 C35 1.459(3) . ?
N02 C36 1.461(3) . ?
C09 C08 1.335(3) . ?
C09 H09 0.9500 . ?
C19 C20 1.370(3) . ?
C19 C24 1.399(3) . ?
C19 H19 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C03 C04 1.383(3) . ?
C03 C02 1.407(3) . ?
C13 C14 1.390(3) . ?
C13 C12 1.395(3) . ?
C22 C21 1.393(3) . ?
C22 H22 0.9500 . ?
C32 C33 1.380(3) . ?
C32 C31 1.401(3) . ?
C32 H32 0.9500 . ?
C31 C30 1.403(3) . ?
C20 C21 1.398(3) . ?
C25 C26 1.473(3) . ?
C25 C24 1.487(3) . ?
C33 H33 0.9500 . ?
C08 H08 0.9500 . ?
C06 C05 1.389(3) . ?
C29 C30 1.382(3) . ?
C29 H29 0.9500 . ?
C26 C27 1.336(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C04 C05 1.385(3) . ?
C04 H04 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C05 H05 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C03 O02 C16 117.24(15) . . ?
C13 N01 C18 113.44(15) . . ?
C13 N01 C17 115.49(16) . . ?
C18 N01 C17 110.48(17) . . ?
C21 O04 C34 116.95(16) . . ?
C29 C28 C33 117.44(17) . . ?
C29 C28 C27 119.02(18) . . ?
C33 C28 C27 123.54(18) . . ?
O01 C07 C08 121.25(17) . . ?
O01 C07 C06 120.04(17) . . ?
C08 C07 C06 118.71(16) . . ?
C02 C01 C06 120.31(17) . . ?
C02 C01 H01 119.8 . . ?
C06 C01 H01 119.8 . . ?
C11 C10 C15 118.03(17) . . ?
C11 C10 C09 119.09(17) . . ?
C15 C10 C09 122.82(17) . . ?
C22 C23 C24 121.20(18) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C31 N02 C35 117.12(17) . . ?
C31 N02 C36 116.98(17) . . ?
C35 N02 C36 111.55(18) . . ?
C08 C09 C10 126.06(18) . . ?
C08 C09 H09 117.0 . . ?
C10 C09 H09 117.0 . . ?
C20 C19 C24 120.42(18) . . ?
C20 C19 H19 119.8 . . ?
C24 C19 H19 119.8 . . ?
C12 C11 C10 120.43(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O02 C03 C04 125.10(17) . . ?
O02 C03 C02 117.01(16) . . ?
C04 C03 C02 117.89(17) . . ?
C14 C13 C12 116.55(17) . . ?
C14 C13 N01 122.94(17) . . ?
C12 C13 N01 120.46(17) . . ?
C23 C22 C21 120.09(19) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C33 C32 C31 122.21(19) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C32 C31 C30 116.05(17) . . ?
C32 C31 N02 122.43(18) . . ?
C30 C31 N02 121.46(18) . . ?
C19 C20 C21 121.28(17) . . ?
C19 C20 Cl03 119.76(15) . . ?
C21 C20 Cl03 118.95(15) . . ?
O03 C25 C26 120.98(18) . . ?
O03 C25 C24 119.43(17) . . ?
C26 C25 C24 119.58(17) . . ?
C23 C24 C19 118.44(18) . . ?
C23 C24 C25 122.91(17) . . ?
C19 C24 C25 118.57(17) . . ?
C32 C33 C28 121.00(19) . . ?
C32 C33 H33 119.5 . . ?
C28 C33 H33 119.5 . . ?
C09 C08 C07 120.63(18) . . ?
C09 C08 H08 119.7 . . ?
C07 C08 H08 119.7 . . ?
C01 C02 C03 121.59(16) . . ?
C01 C02 Cl01 119.42(14) . . ?
C03 C02 Cl01 119.00(14) . . ?
C05 C06 C01 118.26(17) . . ?
C05 C06 C07 123.31(17) . . ?
C01 C06 C07 118.43(17) . . ?
C30 C29 C28 121.19(18) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C27 C26 C25 120.79(18) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C29 C30 C31 121.97(18) . . ?
C29 C30 Cl04 116.85(15) . . ?
C31 C30 Cl04 121.11(14) . . ?
C26 C27 C28 127.55(19) . . ?
C26 C27 H27 116.2 . . ?
C28 C27 H27 116.2 . . ?
C15 C14 C13 121.99(18) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
O04 C21 C22 124.70(19) . . ?
O04 C21 C20 116.75(17) . . ?
C22 C21 C20 118.55(18) . . ?
C11 C12 C13 122.18(17) . . ?
C11 C12 Cl02 117.53(14) . . ?
C13 C12 Cl02 120.18(14) . . ?
C03 C04 C05 120.59(18) . . ?
C03 C04 H04 119.7 . . ?
C05 C04 H04 119.7 . . ?
C14 C15 C10 120.75(18) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O02 C16 H16A 109.5 . . ?
O02 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O02 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C04 C05 C06 121.35(18) . . ?
C04 C05 H05 119.3 . . ?
C06 C05 H05 119.3 . . ?
N02 C35 H35A 109.5 . . ?
N02 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N02 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O04 C34 H34A 109.5 . . ?
O04 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O04 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N01 C17 H17A 109.5 . . ?
N01 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N01 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N02 C36 H36A 109.5 . . ?
N02 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N02 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N01 C18 H18C 109.5 . . ?
N01 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
N01 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C10 C09 C08 -161.12(19) . . . . ?
C15 C10 C09 C08 15.9(3) . . . . ?
C15 C10 C11 C12 -2.3(3) . . . . ?
C09 C10 C11 C12 174.92(17) . . . . ?
C16 O02 C03 C04 -1.1(3) . . . . ?
C16 O02 C03 C02 178.41(17) . . . . ?
C18 N01 C13 C14 104.3(2) . . . . ?
C17 N01 C13 C14 -24.7(3) . . . . ?
C18 N01 C13 C12 -78.4(2) . . . . ?
C17 N01 C13 C12 152.60(19) . . . . ?
C24 C23 C22 C21 -0.7(3) . . . . ?
C33 C32 C31 C30 -2.0(3) . . . . ?
C33 C32 C31 N02 -179.07(18) . . . . ?
C35 N02 C31 C32 14.5(3) . . . . ?
C36 N02 C31 C32 -121.9(2) . . . . ?
C35 N02 C31 C30 -162.48(18) . . . . ?
C36 N02 C31 C30 61.1(3) . . . . ?
C24 C19 C20 C21 0.7(3) . . . . ?
C24 C19 C20 Cl03 -178.56(14) . . . . ?
C22 C23 C24 C19 0.9(3) . . . . ?
C22 C23 C24 C25 -175.89(17) . . . . ?
C20 C19 C24 C23 -0.9(3) . . . . ?
C20 C19 C24 C25 176.05(17) . . . . ?
O03 C25 C24 C23 162.46(19) . . . . ?
C26 C25 C24 C23 -16.3(3) . . . . ?
O03 C25 C24 C19 -14.3(3) . . . . ?
C26 C25 C24 C19 166.92(17) . . . . ?
C31 C32 C33 C28 -1.3(3) . . . . ?
C29 C28 C33 C32 2.5(3) . . . . ?
C27 C28 C33 C32 -177.24(18) . . . . ?
C10 C09 C08 C07 177.54(17) . . . . ?
O01 C07 C08 C09 21.1(3) . . . . ?
C06 C07 C08 C09 -158.26(18) . . . . ?
C06 C01 C02 C03 0.5(3) . . . . ?
C06 C01 C02 Cl01 -179.15(15) . . . . ?
O02 C03 C02 C01 -179.13(17) . . . . ?
C04 C03 C02 C01 0.4(3) . . . . ?
O02 C03 C02 Cl01 0.6(2) . . . . ?
C04 C03 C02 Cl01 -179.93(15) . . . . ?
C02 C01 C06 C05 -1.2(3) . . . . ?
C02 C01 C06 C07 179.55(17) . . . . ?
O01 C07 C06 C05 -176.10(19) . . . . ?
C08 C07 C06 C05 3.3(3) . . . . ?
O01 C07 C06 C01 3.1(3) . . . . ?
C08 C07 C06 C01 -177.48(17) . . . . ?
C33 C28 C29 C30 -0.3(3) . . . . ?
C27 C28 C29 C30 179.48(17) . . . . ?
O03 C25 C26 C27 -10.5(3) . . . . ?
C24 C25 C26 C27 168.26(18) . . . . ?
C28 C29 C30 C31 -3.2(3) . . . . ?
C28 C29 C30 Cl04 173.91(15) . . . . ?
C32 C31 C30 C29 4.2(3) . . . . ?
N02 C31 C30 C29 -178.65(17) . . . . ?
C32 C31 C30 Cl04 -172.78(14) . . . . ?
N02 C31 C30 Cl04 4.4(3) . . . . ?
C25 C26 C27 C28 179.02(18) . . . . ?
C29 C28 C27 C26 171.49(19) . . . . ?
C33 C28 C27 C26 -8.8(3) . . . . ?
C12 C13 C14 C15 -2.3(3) . . . . ?
N01 C13 C14 C15 175.08(19) . . . . ?
C34 O04 C21 C22 5.1(3) . . . . ?
C34 O04 C21 C20 -175.39(17) . . . . ?
C23 C22 C21 O04 179.99(18) . . . . ?
C23 C22 C21 C20 0.5(3) . . . . ?
C19 C20 C21 O04 179.98(17) . . . . ?
Cl03 C20 C21 O04 -0.8(2) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
Cl03 C20 C21 C22 178.78(15) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C10 C11 C12 Cl02 -175.45(14) . . . . ?
C14 C13 C12 C11 1.6(3) . . . . ?
N01 C13 C12 C11 -175.86(17) . . . . ?
C14 C13 C12 Cl02 177.65(15) . . . . ?
N01 C13 C12 Cl02 0.2(3) . . . . ?
O02 C03 C04 C05 178.87(19) . . . . ?
C02 C03 C04 C05 -0.6(3) . . . . ?
C13 C14 C15 C10 0.8(3) . . . . ?
C11 C10 C15 C14 1.6(3) . . . . ?
C09 C10 C15 C14 -175.50(19) . . . . ?
C03 C04 C05 C06 -0.1(3) . . . . ?
C01 C06 C05 C04 1.0(3) . . . . ?
C07 C06 C05 C04 -179.81(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_preparation       Luminescent
